Russia’s help will be crucial for President Barack Obama in addressing the crisis in Syria and the Iran nuclear standoff, but President Vladimir Putin is playing hard to get. Since resuming the presidency three weeks ago after a four-year, constitutionally mandated sabbatical in the role of Prime Minister, Putin pointedly snubbed the G-8 summit hosted by Obama at Camp David, instead sending Prime Minister Dmitri Medvedev. Obama and Putin have finally agreed on a date and venue for a tête-à-tête, even if the timing is a little fraught: they plan to huddle on the sidelines of G-20 meeting in the Mexican city of Los Cabos from June 18 to 19. Curiously enough, the same dates have been chosen for the next round of talks between Iran and the P5+1 (the U.S., Britain, France, Germany, Russia and China), which will be held in Moscow.

There will be considerable pressure for the Moscow meetings to generate an agreement that will keep the diplomatic process going — a tall order given the gulf between Iran and its interlocutors revealed in last week’s talks in Baghdad. The Iranians were shocked by the P5+1 offering no prospect of relief from sanctions targeting Iran’s oil and banking sector, even if it agreed to the confidence-building steps proposed by the world powers. (They asked Iran to halt uranium enrichment to 20% purity, ship out its stockpile of such material and cease operations at its Fordow enrichment plant buried deep in a mountainside near Qom.) Those steps would buy only minor concessions from Western powers, which made it clear that the only way to stop the unprecedented European oil embargo and measures against Iran’s banks was to heed U.N. Security Council demands that it freeze all uranium enrichment.

The new sanctions take effect on July 1, just two weeks after the Moscow talks, and if they are demonstrably implemented, it may become more difficult politically for Iran’s leaders to stay at the table. (Any inclination toward defiance will be reinforced by a belief in Tehran that Western leaders, given their economic crisis, need the diplomacy as much, if not more, than Iran does.) Iran remains steadfast in refusing the demand that it halt all enrichment and refuses to engage in any process designed to reach that end point. As a result, Iranian officials warned that they were being offered no incentive to take confidence-building steps on issues like 20% enrichment.

Obama’s election-season concerns work against the idea of concessions to Iran, and Israel is pushing him to take an even tougher line. Prime Minister Benjamin Netanyahu on Tuesday branded anything less than a complete halt to all enrichment in Iran an unacceptable outcome. And, of course, the minimum being demanded by the Israelis far exceeds the maximum Iran would likely concede. Israel’s Deputy Prime Minister Moshe Yaalon told an Israel radio station that the talks were simply giving Iran more time: “To my regret, I don’t see any sense of urgency,” Yaalon was quoted as saying, “and perhaps it is even in the interest of some players in the West to stretch out the time, which would certainly square with the Iranian interest.”

Yaalon may not be wrong: while the Israelis tap their watches, most Western leaders don’t share their minutes-to-midnight assessment and oppose military action at a point where Iran is accumulating the means to build nuclear weapons, but hasn’t yet taken a decision to build them. Still, the Israeli pressure tends to reverberate on Capitol Hill, restraining Obama’s political room for maneuver on the Iran issue. The President certainly wants to avoid being steamrollered into any confrontation. If he’s to show progress on his own strategy for dealing with Iran, he’ll need Putin’s help.

Iran is at the negotiating table partly because its presumptive allies, Russia and China, demand that it take steps to demonstrate the peaceful intent of its nuclear program. The current negotiating framework — which proposes step-by-step reciprocal moves to ease the standoff — was originally devised by the Russians. Hope of persuading Iran to take measures to ease the danger of confrontation has always rested more on the position of Iran’s friends and most important trading partners, than on the tough line taken by Western governments that Tehran is hardwired to defy. Russian Foreign Minister Sergei Lavrov last week insisted that Iranian steps toward meeting international concerns should be greeted with an easing of sanctions. The ability of the P5+1 to launch a process of reciprocal steps with Iran may depend in no small part on Russia’s ability to fashion compromises that heed the political concerns from both sides of the table.

But Russia’s interventions on Iran — just as its stance on Syria — will be driven by its own interests and Putin’s reading of them. Putin is looking to reassert Russian influence, particularly in the Middle East, and that means curbing Washington’s ability to resolve a crisis like Syria. Though Russia has lately been critical of the Assad regime, it is always careful to apportion equal blame for Syrian violence on the armed opposition and those supplying their weapons. It appears unlikely to lend its weight to any regime-change effort or to allow legal authorization for military action via the U.N.

Russia’s cooperation on Syria and Iran is likely to be based, first and foremost, on securing its own interests in how those crises are resolved. But cooperation on solving problems that are more pressing for Washington than for Moscow may also see Putin demand a quid pro quo on Russian concerns closer to home. President George W. Bush, on first meeting Putin in 2001, claimed to have looked the Russian in the eye and gotten “a sense of his soul,” proclaiming him a “trustworthy man.” Obama is more likely to discover in Los Cabos that his Russian counterpart is not exactly a cheap date.

Tony Karon is a senior editor at TIME, where he has covered international conflicts in the Middle East, Asia, and the Balkans since 1997. A native of South Africa, he now resides with his family in Brooklyn, New York.